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Regioselective Hydroboration of Terminal Alkenes with the Addition of Triflic Acid to Borane
1Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
Abstract:
The preactivation of borane dimethyl sulfide complex with triflic acid formed a highly reactive hydroborating agent, H2BOTf. This reagent, generated in situ, reacted with terminal alkenes with higher regioselectivity than for borane dimethyl sulfide complex, favoring the primary alcohol products with regioisomeric ratios of up to 99:1. Oxidation of boranes could be performed with t-BuOOH and CsOH·H2O, which, in the case of hindered boranes, was faster and higher-yielding than reactions using standard oxidation conditions (H2O2 and NaOH).
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